4-Bromobutyryl chloride → HCID 86695513, compound

HRID 1487556Notes

Reaction equation

HRID 1487556 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].[F:8][CH:9]([F:36])[C:10]([NH:12][C@H:13]([CH2:34][F:35])[C@H:14]([OH:33])[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:22]=[N:23][C:24]([CH2:27][NH:28][S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:26]=2)=[CH:17][CH:16]=1)=[O:11].C(N(CC)C(C)C)(C)C>CN(C)C1C=CN=CC=1.CN(C)C=O>[Br:1][CH2:2][CH2:3][CH2:4][C:5]([O:33][C@H:14]([C:15]1[CH:16]=[CH:17][C:18]([C:21]2[CH:22]=[N:23][C:24]([CH2:27][NH:28][S:29]([CH3:32])(=[O:30])=[O:31])=[CH:25][CH:26]=2)=[CH:19][CH:20]=1)[C@H:13]([NH:12][C:10](=[O:11])[CH:9]([F:8])[F:36])[CH2:34][F:35])=[O:6]

Participants

6

Reactant 3

HCID 702254-Bromobutyryl chlorideHCID 81531DiisopropylethylamineHCID 86695514HCID 86695514, compound

Product 1

HCID 86695513HCID 86695513, compoundYield 59.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

4-Bromobutanoyl chloride (29.6 μL, 0.255 mmol) is added dropwise to a stirred solution of 2,2-difluoro-N-{(1S,2R)-1-(fluoromethyl)-2-hydroxy-2-[4-(6-{[(methylsulfonyl)amino]methyl}pyridin-3-yl)phenyl]ethyl}acetamide (100.0 mg, 0.232 mmol), N,N-diisopropylethylamine (48.4 μL, 0.278 mmol), and 4-dimethylaminopyridine (11.3 mg, 0.093 mmol) in N,N-dimethylformamide (1.00 mL) at rt. The reaction mixture is stirred for 1 hour before being concentrated. The residue was purified by CombiFlash (4 g column) eluting with 0-100% ethyl acetate to yield the title compound (80.0 mg, 59%) as a yellow foam. MS (ESI+) m/z 581.7 [M+H].

Workup

  1. concentrationbefore being concentrated
  2. customThe residue was purified by CombiFlash (4 g column)
  3. washeluting with 0-100% ethyl acetate

Sources & evidence

ORD record
ord-75c66e0f0d3e458e883deb5272392d7c
Source dataset
uspto-grants-2016_08
Patent number
US09428528B2

Reaction notes

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